4-(3-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)prop-1-enyl)benzoic acid

ID: ALA4637186

PubChem CID: 7503866

Max Phase: Preclinical

Molecular Formula: C18H13NO5

Molecular Weight: 323.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1COc2ccc(C(=O)/C=C/c3ccc(C(=O)O)cc3)cc2N1

Standard InChI:  InChI=1S/C18H13NO5/c20-15(7-3-11-1-4-12(5-2-11)18(22)23)13-6-8-16-14(9-13)19-17(21)10-24-16/h1-9H,10H2,(H,19,21)(H,22,23)/b7-3+

Standard InChI Key:  FTYOUNWWAUZCCW-XVNBXDOJSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   19.5575   -2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5564   -3.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2644   -4.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9741   -3.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9713   -2.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2626   -2.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8497   -2.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4343   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4341   -1.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6824   -4.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6837   -4.9245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3895   -3.6976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7275   -2.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0194   -2.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3123   -2.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3120   -3.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0248   -4.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7290   -3.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6047   -2.4706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6050   -4.1071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8966   -3.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8953   -2.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1868   -2.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  9 14  1  0
 16 20  1  0
 20 23  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4637186

   4-[(E)-3-oxo-3-(3-oxo-4H-1,4-benzoxazin-6-yl)prop-1-enyl]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 323.30

Molecular Weight (Monoisotopic): 323.0794

AlogP: 2.61

#Rotatable Bonds: 4

Polar Surface Area: 92.70

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.11

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: -0.76

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -0.33

References

1. de Souza ACA, Mori M, Sens L, Rocha RF, Tizziani T, de Souza LFS, Domeneghini Chiaradia-Delatorre L, Botta M, Nunes RJ, Terenzi H, Menegatti ACO..  (2020)  A chalcone derivative binds a putative allosteric site of YopH: Inhibition of a virulence factor of Yersinia.,  30  (16): [PMID:32631548] [10.1016/j.bmcl.2020.127350]

Source

Source(1):

• Scientific Literature